5-[2-(5-Chloro-2-methoxy-phenyl)-2-oxo-ethylcarbamoyl]-pentanoic acid methyl ester → 5-[5-(5-Chloro-2-methoxy-phenyl)-oxazol-2-yl]-pentanoic acid methyl ester

HRID 1616585Notes

Reaction equation

HRID 1616585 reaction equation
[CH3:1][O:2][C:3](=[O:23])[CH2:4][CH2:5][CH2:6][CH2:7][C:8](=[O:22])[NH:9][CH2:10][C:11]([C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=1[O:20][CH3:21])=O>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:1][O:2][C:3](=[O:23])[CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[O:22][C:11]([C:13]2[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=2[O:20][CH3:21])=[CH:10][N:9]=1

Participants

4

Reactant 1

HCID 684924995-[2-(5-Chloro-2-methoxy-phenyl)-2-oxo-ethylcarbamoyl]-pentanoic acid methyl ester

Product 1

HCID 591677555-[5-(5-Chloro-2-methoxy-phenyl)-oxazol-2-yl]-pentanoic acid methyl esterYield 49.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Dissolve 5-[2-(5-Chloro-2-methoxy-phenyl)-2-oxo-ethylcarbamoyl]-pentanoic acid methyl ester (9.39 g, 27.47 mmol) and 4-(dimethylamino)pyridine (6.54 g, 53.53 mmol) in 250 mL of CH2Cl2 and cool the reaction mixture in an ice bath. Add triphenylphosphinedibromide (22.54 g, 53.40 mmol) to the reaction portionwise over 15 minutes. Raise the reaction to ambient temperature and allow it to stir for 17 hours. Wash the reaction with water (1×) and brine (2×). Dry the organic layers with MgSO4. Filter off the drying agent and concentrate in vacuo to afford a crude residue. Purify the residue using silica gel chromatography eluting with hexanes/ethyl acetate mixtures to afford 4.38 g of the titled product (49%): mass spectrum: m/z=324.1 (M+H).

Workup

  1. temperaturecool the reaction mixture in an ice bath
  2. additionAdd triphenylphosphinedibromide (22.54 g, 53.40 mmol)
  3. customto the reaction portionwise over 15 minutes
  4. temperatureRaise
  5. customthe reaction to ambient temperature
  6. washWash
  7. customthe reaction with water (1×) and brine (2×)
  8. dry with materialDry the organic layers with MgSO4
  9. filtrationFilter off the drying agent
  10. concentrationconcentrate in vacuo
  11. customto afford a crude residue
  12. customPurify the residue
  13. washeluting with hexanes/ethyl acetate

Sources & evidence

ORD record
ord-3dd826df98b146c386db1d56ea5d7931
Source dataset
uspto-grants-2014_07
Patent number
US08765796B2

Reaction notes

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